Carboxamides as fungicides in agriculture

ABSTRACT

The invention concerns novel carboxamides of formula (I) wherein A is (A1), (A2), (A3), (A4), (A5); Q is (Q1), (Q2), (Q3), (Q4), (Q5), (Q6); R 1  is CH 2  R 2 , CH 2 CH═CHR 2 , CH═C═CHR 2  or COR 3 ; R 2  is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, COOC 1 -C 4 alkyl, COOC 3 -C 6 alkenyl, COOC 3 -C 6 alkynyl or CN; R 3  is C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted by halogen, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; or is C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy; C 3 -C 6 alkenyloxy or C 3 -C 6 haloalkenyloxy; C 3 -C 6 haloalkenyloxy; C 3 -C 6 alkynyloxy or C 3 -C 6 haloalkynyloxy; R 4  is methyl, CF 2 Cl, CF 3 , CF 2 H, CFH 2 , Cl or Br, R 5  is methyl, CF 3 , CH 2 OCH 3  or CH 2 OCF 3 ; R 6  is hydrogen, fluoro, CF 3  or methyl; R 7  is hydrogen, methyl or halogen; and Z is phenyl, halophenyl, C 5 -C 7 cycloalkyl, C 5 -C 7 cycloalkyl substituted by C 1 -C 3 alkyl, C 1 C 3 haloalkyl or halogen, or a group of the form —CHR 8 —CH 2 —CHR 9 R 10  wherein R 8 , R 9  and R 10  are independently of each other C 1 -C 3 alkyl. The novel compounds have plant-protective properties and are suitable for protecting plants against infestation by phytopathogenic microorganisms, in particular fungi.

This application is a 371 of International Application No.PCT/EP02/00717 filed Jan. 24, 2002, which claims priority to GB0101996.7, filed Jan. 25, 2001.

The present invention relates to novel carboxamides which havemicrobicidal activity, in particular fungicidal activity. The inventionalso relates to the preparation of these substances, to agrochemicalcompositions which comprise at least one of the novel compounds asactive ingredient, to the preparation of the compositions mentioned, toa method of protecting plants against attack or infestation byphytopathogenic organisms, preferably fungi, by applying the novelcompounds as specified hereinafter to a part and/or the site of a plantand to the use of said novel compounds or compositions thereof inagriculture and horticulture for controlling or preventing infestationof plants by phytopathogenic microorganisms, preferably fungi.

The carboxamides of the present invention have the general formula I

-   R₁, is

CH₂CH═CHR₂, CH═C═CHR₂ or COR₃;

-   R₂ is hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl,    C₂-C₆alkynyl, C₃-C₇cycloalkyl,-   COOC₁-C₄alkyl, COOC₃-C₆alkenyl, COOC₃-C₆alkynyl or CN;-   R₃ is C₁-C₆alkyl, C₁-C₆alkyl substituted by halogen, C₁-C₆alkoxy or    C₁-C₆haloalkoxy; or is-   C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkoxy, C₁-C₆haloalkoxy;    C₃-C₆alkenyloxy or-   C₃-C₆haloalkenyloxy; C₃-C₆alkynyloxy or C₃-C₆haloalkynyloxy;-   R₄ is methyl, CF₂Cl, CF₃, CF₂H, CFH₂, Cl or Br;-   R₅ is methyl, CF₃, CH₂OCH₃ or CH₂OCF₃;-   R₆ is hydrogen, fluoro, CF₃ or methyl;-   R₇ is hydrogen, methyl or halogen, and-   Z is phenyl, halophenyl, C₅-C₇cycloalkyl, C₅-C₇cycloalkyl    substituted by C₁-C₃alkyl,-   C₁-C₃haloalkyl or halogen, or a group of the form

wherein R₈, R₉ and R₁₀ are independently of each other C₁-C₃alkyl.

Surprisingly, it has now been found that the compounds of formula Iexhibit improved biological properties which render them more suitablefor the practical use in agriculture and horticulture.

Where asymmetrical carbon atoms are present in the compounds of formulaI, these compounds are in optically active form. The invention relatesto the pure isomers, such as enantiomers and diastereomers, as well asto all possible mixtures of isomers, e.g. mixtures of diastereomers,racemates or mixture of racemates.

Within the present specification alkyl denotes methyl, ethyl, n-propyl,n-butyl, n-pentyl, n-hexyl, isopropyl, isobutyl, sec.-butyl,tert.-butyl, isopentyl, neopentyl and isohexyl. Non-branched alkyl ispreferred. Alkyl as part of other radicals such as alkoxy, haloalkyl,etc. is understood in an analogous way. Halogen will be understoodgenerally as meaning fluoro, chloro, bromo or iodo. Fluoro, chloro orbromo are preferred meanings. Halogen as part of other radicals such ashaloalkyl, haloalkoxy, etc. is understood in an analogous way.

Haloalkyl is preferably C₁-C₆alkyl, more preferably lower alkyl, that islinear or branched and is substituted by one or more, for example in thecase of halo-ethyl up to five, halogen atoms, especially fluorine. Asexample is trifluoromethyl.

Haloalkoxy is preferably C₁-C₆alkoxy, that is linear or branched andthat is substituted by one or more halogen atoms, especially fluorine;trifluoromethoxy, perfluoroethyl and 1,1,2,2-tetrafluoroethoxy arepreferred.

Cycloalkyl is, depending on the ring size, cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl or cycloheptyl.

Alkenyl will be understood as meaning straight-chain or branched alkenylsuch as allyl, methallyl, 1-methylvinyl or but-2-en-1-yl. Preferredalkenyl radicals contain 3 to 4 carbon atoms in the chain, i.e. allyl or2-butenyl. This also applies where alkenyl is part of haloalkenyl,alkenyloxy or haloalkenyloxy.

Alkynyl can likewise, in accordance with the number of carbon atoms, bestraight-chain or branched and is typically propargyl, but-2-yn-1-yl orbut-1-yn-3-yl. The same definitions apply where alkynyl is part ofalkynyloxy or haloalkynyloxy.

Among the compounds of formula I according to the present invention thefollowing groups of compounds are preferred. These groups are thosewherein

-   A is A1, A2, A3, A4 or A5, or-   A is A1, A2 or A3, or-   A is A1 or A2, or-   Q is Q1, Q2, Q3, Q4, Q5 or Q6, or-   Q is Q5 or Q6, or-   Q is Q1 or Q6, or-   R₁ is

CH₂CH═CHR₂, CH═C═CHR₂or COR₃, or

-   R₂ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₂-C₄alkenyl,    C₂-C₄alkynyl, C₃-C₆cycloalkyl, COOC₁-C₄alkyl, COOC₃-C₄alkenyl or    COOC₃-C₄alkynyl, or-   R₂ is hydrogen ; or-   R₃ is C₁-C₆alkyl, C₁-C₆alkyl substituted by fluoro, chloro, bromo,    C₁-C₄alkoxy or-   C₁-C₄haloalkoxy; or is C₁-C₄alkoxy, C₁-C₄haloalkoxy; C₃-C₄alkenyloxy    or C₃-C₆alkynyloxy; or-   R₃ is C₁-C₄alkyl, C₁-C₄alkoxy-C₁-C₄alkyl or C₁-C₄alkoxy; or-   R₃ is C₁-C₃alkyl, C₁-C₃alkoxy-methyl or C₁-C₃alkoxy; or-   R₄ is methyl, CF₂Cl, CF₃, CF₂H, CFH₂, Cl or Br, or-   R₅ is methyl, CF₃, CH₂OCH₃ or CH₂OCF₃, or-   R₆ is hydrogen, fluoro, CF₃ or methyl, or-   R₇ is hydrogen, methyl or halogen, or-   Z is phenyl, halophenyl, C₅-C₇cycloalkyl unsubstituted or    substituted by C₁-C₃alkyl,-   C₁-C₃haloalkyl or halogen, or a group of the form

wherein R₈, R₉ and R₁₀ are independently of each other C₁-C₃alkyl, or

-   Z is phenyl, halophenyl or C₅-C₇cycloalkyl unsubstituted or    substituted by C₁-C₃alkyl, C₁-C₃haloalkyl or halogen, or-   Z is a group of the form

wherein R₈, R₉ and R₁₀ are independently of each other C₁-C₃alkyl.

Within the group of compounds of formula I, those compounds arepreferred wherein

-   A is A1, A2, A3, A4 or A5;-   Q is Q1, Q2, Q3, Q4, Q5 or Q6;-   R₁ is

CH₂CH═CHR₂, CH═C═CHR₂or COR₃;

-   R₂ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₂-C₄alkenyl,    C₂-C₄alkynyl, C₃-C₆cycloalkyl, COOC₁-C₄alkyl, COOC₃-C₄alkenyl or    COOC₃-C₄alkynyl;-   R₃ is C₁-C₆alkyl, C₁-C₆alkyl substituted by fluoro, chloro, bromo,    C₁-C₆alkoxy or C₁-C₆haloalkoxy; or is C₁-C₄alkoxy, C₁-C₄haloalkoxy;    C₃-C₄alkenyloxy or C₃-C₆haloalkynyloxy;-   R₄ is methyl, CF₂Cl, CF₃, CF₂H, CFH₂, Cl or Br;-   R₅ is methyl, CF₃, CH₂OCH₃ or CH₂OCF₃;-   R₆ is hydrogen, fluoro, CF₃ or methyl;-   R₇ is hydrogen, methyl or halogen; and-   Z is phenyl, halophenyl, C₅-C₇cycloalkyl unsubstituted or    substituted by C₁-C₃alkyl, C₁C₃haloalkyl or halogen, or a group of    the form

wherein R₈, R₉ and R₁₀ are independently of each other C₁-C₃alkyl(subgroup B1).

Within the subgroup B1 of compounds of formula I those compounds arepreferred wherein

-   A is A1, A2, A3, A4 or A5;-   Q is Q1;-   R₁ is

CH₂CH═CHR₂, CH═C═CHR₂ or COR₃;

-   R₂ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₂-C₄alkenyl,    C₂-C₄alkynyl, C₃-C₆cycloalkyl, COOC₁-C₄alkyl, COOC₃-C₄alkenyl or    COOC₃-C₄alkynyl;-   R₃ is C₁-C₆alkyl, C₁-C₆alkyl substituted by fluoro, chloro, bromo,    C₁-C₆alkoxy or C₁-C₆haloalkoxy; or is C₁-C₄alkoxy, C₁-C₄haloalkoxy;    C₃-C₄alkenyloxy or C₃-C₆haloalkynyloxy;-   R₄ is methyl, CF₂Cl, CF₃, CF₂H, CFH₂, Cl or Br;-   R₅ is methyl, CF₃, CH₂OCH₃ or CH₂OCF₃;-   R₆ is hydrogen, fluoro, CF₃ or methyl;-   R₇ is hydrogen, methyl or halogen; and-   Z is phenyl, halophenyl, C₅-C₇cycloalkyl unsubstituted or    substituted by C₁-C₃alkyl, C₁-C₃haloalkyl or halogen, or a group of    the form

wherein R₈, R₉ and R₁₀ are independently of each other C₁-C₃alkyl(subgroup B2).

Within the subgroup B2 are those compounds more preferred wherein

-   A is A1, A2, A3, A4 or A5;-   Q is Q1;-   R₁ is

CH₂CH═CHR₂, CH═C═CHR₂ or COR₃;

-   R₂ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₂-C₄alkenyl,    C₂-C₄alkynyl, C₃-C₆cycloalkyl, COOC₁-C₄alkyl, COOC₃-C₄alkenyl or    COOC₃-C₄alkynyl;-   R₃ is C₁-C₆alkyl, C₁-C₆alkyl substituted by fluoro, chloro, bromo,    C₁-C₆alkoxy or C₁-C₆haloalkoxy; or is C₁-C₄alkoxy, C₁-C₄haloalkoxy;    C₃-C₄alkenyloxy or C₃-C₆haloalkynyloxy;-   R₄ is methyl, CF₂Cl, CF₃, CF₂H, CFH₂, Cl or Br;-   R₅ is methyl, CF₃, CH₂OCH₃ or CH₂OCF₃;-   R₆ is hydrogen, fluoro, CF₃ or methyl;-   R₇ is hydrogen, methyl or halogen; and-   Z is phenyl, halophenyl or a group of the form

wherein R₈, R₉ and R₁₀ are independently of each other C₁-C₃alkyl(subgroup B21).

Within the subgroup B2 are those compounds preferred wherein.

-   A is A1, A2, A3, A4 or A5;-   Q is Q1;-   R₁ is

CH₂CH═CHR₂, CH═C═CHR₂ or COR₃;

-   R₂ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₂-C₄alkenyl,    C₂-C₄alkynyl, C₃-C₆cycloalkyl, COOC₁-C₄alkyl, COOC₃-C₄alkenyl or    COOC₃-C₄alkynyl;-   R₃ is C₁-C₆alkyl, C₁-C₆alkyl substituted by fluoro, chloro, bromo,    C₁-C₆alkoxy or C₁-C₆haloalkoxy; or is C₁-C₄alkoxy, C₁-C₄haloalkoxy;    C₃-C₄alkenyloxy or C₃-C₆haloalkynyloxy;-   R₄ is methyl, CF₂Cl, CF₃, CF₂H, CFH₂, Cl or Br;-   R₅ is methyl, CF₃, CH₂OCH₃ or CH₂OCF₃;-   R₆ is hydrogen, fluoro, CF₃ or methyl;-   R₇ is hydrogen, methyl or halogen; and-   Z is C₅-C₇cycloalkyl unsubstituted or substituted by C₁-C₃alkyl,    C₁-C₃haloalkyl or halogen (subgroup B22).

Another group of compounds of formula I within the subgroup B1 are thosewherein

-   A is A1 or A2;-   Q is Q5 or Q6-   R₁ is

CH₂CH═CHR₂, CH═C═CHR₂ or COR₃;

-   R₂ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₂-C₄alkenyl,    C₂-C₄alkynyl, C₃-C₆cycloalkyl, COOC₁-C₄alkyl, COOC₃-C₄alkenyl or    COOC₃-C₄alkynyl;-   R₃ is C₁-C₆alkyl, C₁-C₆alkyl substituted by fluoro, chloro, bromo,    C₁-C₆alkoxy or C₁-C₆haloalkoxy; or is C₁-C₄alkoxy, C₁-C₄haloalkoxy;    C₃-C₄alkenyloxy or C₃-C₆haloalkynyloxy;-   R₄ is methyl, CF₂Cl, CF₃, CF₂H, CFH₂, Cl or Br;-   R₅ is methyl, CF₃, CH₂OCH₃ or CH₂OCF₃;-   R₆ is hydrogen, fluoro, CF₃ or methyl; and-   R₇ is hydrogen, methyl or halogen (subgroup B3).

Within the subgroup B1 are those compounds of formula I preferredwherein

-   A is A1 or A2;-   Q is Q2, Q3 or Q4;-   R₁ is

CH₂CH═CHR₂, CH═C═CHR₂ or COR₃;

-   R₂ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₂-C₄alkenyl,    C₂-C₄alkynyl, C₃-C₆cycloalkyl, COOC₁-C₄alkyl, COOC₃-C₄alkenyl or    COOC₃-C₄alkynyl;-   R₃ is C₁-C₆alkyl, C₁-C₆alkyl substituted by fluoro, chloro, bromo,    C₁-C₆alkoxy or C₁-C₆haloalkoxy; or is C₁-C₄alkoxy, C₁-C₄haloalkoxy;    C₃-C₄alkenyloxy or C₃-C₆haloalkynyloxy;-   R₄ is methyl, CF₂Cl, CF₃, CF₂H, CFH₂, Cl or Br;-   R₅ is methyl, CF₃, CH₂OCH₃ or CH₂OCF₃;-   R₆ is hydrogen, fluoro, CF₃ or methyl;-   R₇ is hydrogen, methyl or halogen; and-   Z is phenyl, halophenyl, C₅-C₇cycloalkyl unsubstituted or    substituted by C₁-C₃alkyl, C₁-C₃haloalkyl or halogen, or a group of    the form

wherein R₈, R₉ and R₁₀ are independently of each other C₁-C₃alkyl(subgroup B13).

From subgroup B1 are further preferred compounds of formula I wherein

-   A is A1, A2 or A3;-   Q is Q1 or Q6;-   R₁ is

CH₂CH═CHR₂, CH═C═CHR₂ or COR₃;

-   R₂ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₂-C₄alkenyl,    C₂-C₄alkynyl, C₃-C₆cycloalkyl,COOC₁-C₄alkyl, COOC₃-C₄alkenyl or    COOC₃-C₄alkynyl;-   R₃ is C₁-C₆alkyl, C₁-C₆alkyl substituted by fluoro, chloro, bromo,    C₁-C₆alkoxy or C₁-C₆haloalkoxy; or is C₁-C₄alkoxy, C₁-C₄haloalkoxy;    C₃-C₄alkenyloxy or C₃-C₆haloalkynyloxy;-   R₄ is methyl, CF₂Cl, CF₃, CF₂H, CFH₂, Cl or Br;-   R₅ is methyl, CF₃, CH₂OCH₃ or CH₂OCF₃;-   R₆ is hydrogen, fluoro, CF₃ or methyl;-   R₇ is hydrogen, methyl or halogen; and-   Z is phenyl, halophenyl or C₅-C₇cycloalkyl unsubstituted or    substituted by C₁-C₃alkyl, C₁-C₃haloalkyl or halogen (subgroup B4).

In the above listed subgroups further preference is given to thosewherein

-   R₂ is hydrogen; or-   R₃ is C₁-C₄alkyl, C₁-C₄alkoxy-C₁-C₄alkyl or C₁-C₄alkoxy; or-   R₃ is C₁-C₃alkyl, C₁-C₃alkoxy-methyl or C₁-C₃alkoxy; or a group    wherein-   R₂ is hydrogen; and R₃ is C₁-C₃alkyl, C₁-C₃alkoxy-methyl or    C₁-C₃alkoxy.

Preferred individual compounds of the formula I are:

-   1-methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-propargyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-propargyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-acetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-acetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methoxymethyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methoxymethyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methoxymethyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-propargyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methoxymethyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-propargyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methoxymethyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-acetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methoxymethyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-acetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-methoxyacetyl)-(1,1,3-trimethylindan-4-yl)amide,-   1-methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-propargyl)-(1,1,3-trimethylindan-4-yl)amide,-   1-methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid    (2-acetyl)-(1,1,3-trimethylindan-4-yl)amide,-   1-methyl-4-trifluoromethyl-pyrazole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-pyrazole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-pyrazole-3-carboxylic acid    (2-propargyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-pyrazole-3-carboxylic acid    (2-propargyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-pyrazole-3-carboxylic acid    (2-acetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-pyrazole-3-carboxylic acid    (2-acetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methoxymethyl-4-trifluoromethyl-pyrazole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methoxymethyl-4-trifluoromethyl-pyrazole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methoxymethyl-4-trifluoromethyl-pyrazole-3-carboxylic acid    (2-propargyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methoxymethyl-4-trifluoromethyl-pyrazole-3-carboxylic acid    (2-propargyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methoxymethyl-4-trifluoromethyl-pyrazole-3-carboxylic acid    (2-acetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methoxymethyl-4-trifluoromethyl-pyrazole-3-carboxylic acid    (2-acetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methyl-4-difluoromethyl-pyrazole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methyl-4-difluoromethyl-pyrazole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methyl-4-difluoromethyl-pyrazole-3-carboxylic acid    (2-propargyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methyl-4-difluoromethyl-pyrazole-3-carboxylic acid    (2-propargyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methyl-4-difluoromethyl-pyrazole-3-carboxylic acid    (2-acetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methyl-4-difluoromethyl-pyrazole-3-carboxylic acid    (2-acetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methoxymethyl-4-difluoromethyl-pyrazole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methoxymethyl-4-difluoromethyl-pyrazole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methoxymethyl-4-difluoromethyl-pyrazole-3-carboxylic acid    (2-propargyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methoxymethyl-4-difluoromethyl-pyrazole-3-carboxylic acid    (2-propargyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methoxymethyl-4-difluoromethyl-pyrazole-3-carboxylic acid    (2-acetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methoxymethyl-4-difluoromethyl-pyrazole-3-carboxylic acid    (2-acetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-thiazole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-thiazole-3-carboxylic acid    (2-methoxyacetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-thiazole-3-carboxylic acid    (2-propargyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-thiazole-3-carboxylic acid    (2-propargyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-thiazole-3-carboxylic acid    (2-acetyl)-[2′(4-fluorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-thiazole-3-carboxylic acid    (2-acetyl)-[2′(4-chlorophenyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-1H-pyrrole-carboxylic acid    (2-methoxyacetyl)-[2′-(3-methylcyclohexyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-1H-pyrrole-carboxylic acid    (2-methoxyacetyl)-[2′-(3-ethylcyclohexyl)phenyl]amide,-   1-methyl-4-trifluoromethyl-1H-pyrrole-carboxylic acid    (2-methoxyacetyl)-[2′-(3-trifluoromethylcyclohexyl)phenyl]amide.

The compounds according to formula I may be prepared according to thefollowing reaction scheme.

Surprisingly, it has now been found that the novel compounds of formulaI have, for practical purposes, a very advantageous spectrum ofactivities for protecting plants against diseases that are caused byfungi as well as by bacteria and viruses.

The compounds of formula I can be used in the agricultural sector andrelated fields of use as active ingredients for controlling plant pests.The novel compounds are distinguished by excellent activity at low ratesof application, by being well tolerated by plants and by beingenvironmentally safe. They have very useful curative, preventive andsystemic properties and are used for protecting numerous cultivatedplants. The compounds of formula I can be used to inhibit or destroy thepests that occur on plants or parts of plants (fruit, blossoms, leaves,stems, tubers, roots) of different crops of useful plants, while at thesame time protecting also those parts of the plants that grow later e.g.from phytopathogenic micro-organisms.

It is also possible to use compounds of formula I as dressing agents forthe treatment of plant propagation material, in particular of seeds(fruit, tubers, grains) and plant cuttings (e.g. rice), for theprotection against fungal infections as well as against phytopathogenicfungi occurring in the soil.

The compounds I are, for example, effective against the phytopathogenicfungi of the following classes: Fungi imperfecti (e.g. Botrytis,Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora andAlternaria) and Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia).Additionally, they are also effective against the Ascomycetes classes(e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and ofthe Oomycetes classes (e.g. Phytophthora, Pythium, Plasmopara).Outstanding activity has been observed against powdery mildew (Erysiphespp.). Furthermore, the novel compounds of formula I are effectiveagainst phytopathogenic bacteria and viruses (e.g. against Xanthomonasspp, Pseudomonas spp, Erwinia amylovora as well as against the tobaccomosaic virus).

Within the scope of present Invention, target crops to be protectedtypically comprise the following species of plants: cereal (wheat,barley, rye, oat, rice, maize, sorghum and related species); beet (sugarbeet and fodder beet); pomes, drupes and soft fruit (apples, pears,plums, peaches, almonds, cherries, strawberries, raspberries andblackberries); leguminous plants (beans, lentils, peas, soybeans); oilplants (rape, mustard, poppy, olives, sunflowers, coconut, castor oilplants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers,melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges,lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus,cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae(avocado, cinnamomum, camphor) or plants such as tobacco, nuts, coffee,eggplants, sugar cane, tea, pepper, vines, hops, bananas and naturalrubber plants, as well as ornamentals.

The compounds of formula I are used in unmodified form or, preferably,together with the adjuvants conventionally employed in the art offormulation. To this end they are conveniently formulated in knownmanner to emulsifiable concentrates, coatable pastes, directly sprayableor dilutable solutions, dilute emulsions, wettable powders, solublepowders, dusts, granulates, and also encapsulations e.g. in polymericsubstances. As with the type of the compositions, the methods ofapplication, such as spraying, atomizing, dusting, scattering, coatingor pouring, are chosen in accordance with the intended objectives andthe prevailing circumstances. The compositions may also contain furtheradjuvants such as stabilizers, antifoams, viscosity regulators, bindersor tackifiers as well as fertilizers, micronutrient donors or otherformulations for obtaining special effects.

Suitable carriers and adjuvants can be solid or liquid and aresubstances useful in formulation technology, e.g. natural or regeneratedmineral substances, solvents, dispersants, wetting agents, tackifiers,thickeners, binders or fertilizers. Such carriers are for exampledescribed in WO 97/33890.

The compounds of formula I are normally used in the form of compositionsand can be applied to the crop area or plant to be treated,simultaneously or in succession with further compounds. These furthercompounds can be e.g. fertilizers or micronutrient donors or otherpreparations which influence the growth of plants. They can also beselective herbicides as well as insecticides, fungicides, bactericides,nematicides, molluscicides or mixtures of several of these preparations,if desired together with further carriers, surfactants or applicationpromoting adjuvants customarily employed in the art of formulation.

The compounds of formula I can be mixed with other fungicides, resultingin some cases in unexpected synergistic activities. Such mixtures arenot limited to two active ingredients (one of formula I and one of thelist of other fungicides), but to the contrary many comprise more thanone active ingredient of the component of formula I and more than oneother fungicide. Mixing components which are particularly suited forthis purpose include e.g. azoles, such as azaconazole, BAY 14120,bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole,epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol,hexaconazole, imazalil, imibenconazole, ipconazole, metconazole,myclobutanil, pefurazoate, penconazole, pyrifenox, prochloraz,propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon,triadimenol, triflumizole, triticonazole; pyrimidinyl carbinoles, suchas ancymidol, fenarimol, nuarimol; 2-amino-pyrimidines, such asbupirimate, dimethirimol, ethirimol; morpholines, such as dodemorph,fenpropidine, fenpropimorph, spiroxamine, tridemorph;anilinopyrimidines, such as cyprodinil, mepanipyrim, pyrimethanil;pyrroles, such as fenpiclonil, fludioxonil; phenylamides, such asbenalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace, oxadixyl;benzimidazoles, such as benomyl, carbendazim, debacarb, fuberidazole,thiabendazole; dicarboximides, such as chlozolinate, dichlozoline,iprodione, myclozoline, procymidone, vinclozoline; carboxamides, such ascarboxin, fenfuram, flutolanil, mepronil, oxycarboxin, thifluzamide;guanidines, such as guazatine, dodine, iminoctadine; strobilurines, suchas azoxystrobin, kresoxim-methyl, metominostrobin, SSF-129,trifloxystrobin, picoxystrobin, BAS 500F (proposed name pyraclostrobin),BAS 520; dithiocarbamates, such as ferbam, mancozeb, maneb, metiram,propineb, thiram, zineb, ziram; N-halomethylthiotetrahydrophthalimides,such as captafol, captan, dichlofluanid, fluoromides, folpet,tolyfluanid; Cu-compounds, such as Bordeaux mixture, copper hydroxide,copper oxychloride, copper sulfate, cuprous oxide, mancopper,oxine-copper; nitrophenol-derivatives, such as dinocap,nitrothal-isopropyl; organo-p-derivatives, such as edifenphos,iprobenphos, isoprothiolane, phosdiphen, pyrazophos, tolclofosmethyl;various others, such as acibenzolar-S-methyl, anilazine,benthiavalicarb, blasticidin-S, chinomethionate, chloroneb,chlorothalonil, cyflufenamid, cymoxanil, dichione, diclomezine,dicloran, diethofencarb, dimethomorph, SYP-LI90 (proposed name:flumorph), dithianon, ethaboxam, etridiazole, famoxadone, fenamidone,fenoxanil, fentin, ferimzone, fluazinam, flusulfamide, fenhexamid,fosetyl-aluminium, hymexazol, iprovalicarb, IKF-916 (cyazofamid),kasugamycin, methasulfocarb, metrafenone, nicobifen, pencycuron,phthalide, polyoxins, probenazole, propamocarb, pyroquilon, quinoxyfen,quintozene, sulfur, triazoxide, tricyclazole, triforine, validamycin,zoxamide (RH7281).

A preferred method of applying a compound of formula I, or anagrochemical composition which contains at least one of said compounds,is foliar application. The frequency of application and the rate ofapplication will depend on the risk of infestation by the correspondingpathogen. However, the compounds of formula I can also penetrate theplant through the roots via the soil (systemic action) by drenching thelocus of the plant with a liquid formulation, or by applying thecompounds in solid form to the soil, e.g. in granular form (soilapplication). In crops of water rice such granulates can be applied tothe flooded rice field. The compounds of formula I may also be appliedto seeds (coating) by impregnating the seeds or tubers either with aliquid formulation of the fungicide or coating them with a solidformulation.

The formulation, i.e. the compositions containing the compound offormula I and, if desired, a solid or liquid adjuvant, are prepared inknown manner, typically by intimately mixing and/or grinding thecompound with extenders, e.g. solvents, solid carriers and, optionally,surface active compounds (surfactants).

The agrochemical formulations will usually contain from 0.1 to 99% byweight, preferably from 0.1 to 95% by weight, of the compound of formulaI, 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid orliquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25%by weight, of a surfactant.

Advantageous rates of application are normally from 5 g to 2 kg ofactive ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kga.i./ha, most preferably from 20 g to 600 g a.i./ha. When used as seeddrenching agent, convenient dosages are from 10 mg to 1 g of activesubstance per kg of seeds.

Whereas it is preferred to formulate commercial products asconcentrates, the end user will normally use dilute formulations.

The following non-limiting examples illustrate the above-describedinvention in more detail. Temperatures are given in degrees Celsius. Thefollowing abbreviations are used: m.p.=melting point; b.p.=boilingpoint. “NMR” means nuclear magnetic resonance spectrum. MS stands formass spectrum. “%” is percent by weight, unless correspondingconcentrations are indicated in other units.

EXAMPLE 1 1-Methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acidprop-2-ynyl-(1,1,3-trimethylindan-4-yl)amide

To a solution of 0.49 g (1.4 mmol) of compound (A) in 10 mltetrahydrofuran is added 67 mg (1.5 mmol) 55%-sodium hydride and thereaction mixture is stirred for 2 hours. Then 0.12 ml (1.6 mmol)propargyl bromide is added and stirring is continued for 1 hour. Afteraddition of ethylacetate, the organic phase is washed once with waterand once with sodium chloride solution, dried over sodium sulfate andthe solvent is removed. The obtained1-methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acidprop-2-ynyl-(1,1,3-trimethylindan-4-yl)amide (compound 10.3) isrecrystallised from dichloromethane/hexane; m.p. 142-144° C.

EXAMPLE 2 1-Methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid(2-methoxyacetyl)-(1,1,3-trimethylindan-4-yl)amide

To 1.0 g (5.7 mmol) 4-amino-1,1,3-trimethylindane (C) and 0.63 g (6.3mmol) triethylamine in 30 ml tetrahydrofuran is added dropwise asolution of 0.65 g (5.9 mmol) methoxyacetyl chloride in 5 mltetrahydrofuran and the reaction mixture is stirred for 30 minutes.After addition of ethylacetate, the organic phase is washed once withwater and once with sodium chloride solution, dried over sodium sulfateand the solvent is removed. It remains2-methoxy-N-(1,1,3-trimethylindan-4-yl)acetamide (D) as an oil.

A solution of 0.95 g (4.9 mmol) of compound (E) and 0.68 g (5.4 mmol)oxalylchloride in 25 ml dichloromethane is stirred for 3 hours in thepresence of a catalytic amount of dimethylformamide. After removal ofthe solvent, the acid chloride is slowly added to the solution of 1.23 g(4.9 mmol) of compound (D) and 0.22 g (4.9 mmol) 55%-sodium hydride in25 ml tetrahydrofuran, which has been stirred for 3 hours. The reactionmixture is stirred for 16 hours. After addition of ethylacetate, theorganic phase is washed once with water and once with sodium chloridesolution, dried over sodium sulfate and the solvent is removed.Purification by column chromatography over silica gel (eluenthexane:tert.-butylmethylether=7:3) give1-methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid(2-methoxyacetyl)-(1,1,3-trimethylindan-4-yl)amide (compound 10.10) as ayellow oil.

EXAMPLE 3 1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid(4′-bromobiphenyl-2-yl)prop-2-ynyl-amide (Compd. 2.10) and1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid(4′-bromobiphenyl-2-yl)propa-1,2-dienyl-amide (Compd. 2.123)

To a mixture of 137 mg 3.15 mmol sodiumhydride (˜60%) and 15 ml ofabsolute THF a solution of 1.27 g (3.0 mmol) of1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid(4′-bromobiphenyl-2-yl)amide is added slowly and stirred for 20 minutesat +45° C. Then the solution is coold to +20° C. and 410 mg (3.45 mmol)of 3-bromo-1-propyne in 10 ml of THF added slowly. The resulting mixtureis stirred for 20 hours and then 100 ml of ice water is added. Theethylacetate is added and the water phase extracted three times withethylacetate. After drying of the combined organic phase and evaporationof the solvent in a water jet vacuum the crude product is obtained. Theseparation of compounds. 2.10 and 2.123 is accomplished via columnchromatography over silicagel (eluent: hexane/CH₂Cl₂/isoproplyether1:1:1). Compound. 2.123 is obtained in the form of a white powder: m.p.146-149° C. and compound. 2.10 is obtained in the form of a whitepowder: m.p. 171-172° C.

In analogous manner the compounds of the following tables are obtained.

TABLE 1 Intermediates (II)

phys. data Cmpd. no. R₁ Z m.p. ° C. 1.01 —CH₂CH═CH₂ 4-F-phenyl 1.02—CH₂CH═CH₂ 4-Cl-phenyl 1.03 —CH₂CH═CH₂ 4-Br-phenyl 1.04 —CH₂CH═CH₂3-Me-cyclopentyl 1.05 —CH₂CH═CH₂ 4-Me-cyclohexyl 1.06 —CH₂CH═CH₂3-Me-cyclohexyl 1.07 —CH₂CH═CH₂ cycloheptyl 1.08 —CH₂CH═CH₂

1.09 —CH₂C≡CH 4-F-phenyl 1.10 —CH₂C≡CH 4-Cl-phenyl 1.11 —CH₂C≡CH4-Br-phenyl 1.12 —CH₂C≡CH 3-Me-cyclopentyl 1.13 —CH₂C≡CH 4-Me-cyclohexyl1.14 —CH₂C≡CH 3-Me-cyclohexyl 1.15 —CH₂C≡CH cycloheptyl 1.16 —CH₂C≡CH

1.17 —COCH₃ 4-F-phenyl 1.18 —COCH₃ 4-Cl-phenyl 1.19 —COCH₃ 4-Br-phenyl1.20 —COCH₃ 3-Me-cyclopentyl 1.21 —COCH₃ 4-Me-cyclohexyl 1.22 —COCH₃3-Me-cyclohexyl 1.23 —COCH₃ cycloheptyl 1.24 —COCH₃

84-86 1.25 —COCH₂CH₃ 4-F-phenyl 1.26 —COCH₂CH₃ 4-Cl-phenyl 1.27—COCH₂CH₃ 4-br-phenyl 1.28 —COCH₂CH₃ 3-Me-cyclopentyl 1.29 —COCH₂CH₃4-Me-cyclohexyl 1.30 —COCH₂CH₃ 3-Me-cyclohexyl 1.31 —COCH₂CH₃cycloheptyl 1.32 —COCH₂CH₃

1.33 —COCH₂CH₂CH₃ 4-F-phenyl 1.34 —COCH₂CH₂CH₃ 4-Cl-phenyl 1.35—COCH₂CH₂CH₃ 4-Br-phenyl 1.36 —COCH₂CH₂CH₃ cycloheptyl 1.37 —COCH₂CH₂CH₃

1.38 —COcyclopropyl 4-F-phenyl 1.39 —COcyclopropyl 4-Cl-phenyl 1.40—COcyclopropyl 4-Br-phenyl 1.41 —COcyclopropyl cycloheptyl 1.42—COcyclopropyl

1.43 —COCH₂OCH₃ 4-F-phenyl 1.44 —COCH₂OCH₃ 4-Cl-phenyl 1.45 —COCH₂OCH₃4-Br-phenyl 1.46 —COCH₂OCH₃ 3-Me-cyclopentyl 1.47 —COCH₂OCH₃4-Me-cyclohexyl 1.48 —COCH₂OCH₃ 3-Me-cyclohexyl 1.49 —COCH₂OCH₃cycloheptyl 1.50 —COCH₂OCH₃

resin;M⁺ = 249 1.51 —COCH₂OCH₂CH₃ 4-F-phenyl 1.52 —COCH₂OCH₂CH₃4-Cl-phenyl 1.53 —COCH₂OCH₂CH₃ 4-Br-phenyl 1.54 —COCH₂OCH₂CH₃cycloheptyl 1.55 —COCH₂OCH₂CH₃

1.56 —COOCH₃ 4-F-phenyl 1.57 —COOCH₃ 4-Cl-phenyl 1.58 —COOCH₃4-Br-phenyl 1.59 —COOCH₃ 3-Me-cyclopentyl 1.60 —COOCH₃ 4-Me-cyclohexyl1.61 —COOCH₃ 3-Me-cyclohexyl 1.62 —COOCH₃ cycloheptyl 1.63 —COOCH₃

TABLE 2 Pyrazolecarboxamides (Ia)

Cmpd. phys. data no. R₁ R₄ R₅ R₆ Z m.p. ° C. 2.001 —CH₂CH═CH₂ —CF₃ —CH₃H 4-Cl-phenyl  93-95 2.002 —CH₂CH═CH₂ —CF₃ —CH₃ H 4-Br-phenyl 2.003—CH₂CH═CH₂ —CF₃ —CH₃ H 3-Me-cyclopentyl 2.004 —CH₂CH═CH₂ —CF₃ —CH₃ H4-Me-cyclohexyl 2.005 —CH₂CH═CH₂ —CF₃ —CH₃ H 3-Me-cyclohexyl 2.006—CH₂CH═CH₂ —CF₃ —CH₃ H cycloheptyl 2.007 —CH₂CH═CH₂ —CF₃ —CH₃ H

 73-75 2.008 —CH₂C≡CH —CF₃ —CH₃ H 4-F-phenyl 2.009 —CH₂C≡CH —CF₃ —CH₃ H4-Cl-phenyl 169-170 M⁺ = 415 2.010 —CH₂C≡CH —CF₃ —CH₃ H 4-Br-phenyl171-172 2.011 —CH₂C≡CH —CF₃ —CH₃ H 3-Me-cyclopentyl 2.012 —CH₂C≡CH —CF₃—CH₃ H 4-Me-cyclohexyl 2.013 —CH₂C≡CH —CF₃ —CH₃ H 3-Me-cyclohexyl 2.014—CH₂C≡CH —CF₃ —CH₃ H cycloheptyl 2.015 —CH₂C≡CH —CF₃ —CH₃ H

100-102 2.016 —CH₂C≡CH —CF₂H —CH₃ H 4-F-phenyl 127-128 2.017 —CH₂C≡CH—CF₂H —CH₃ H 4-Cl-phenyl 151-152 2.018 —CH₂C≡CH —CF₂H —CH₃ H3-Me-cyclopentyl 2.019 —CH₂C≡CH —CF₂H —CH₃ H 4-Me-cyclohexyl 2.020—CH₂C≡CH —CF₂H —CH₃ H 3-Me-cyclohexyl 2.021 —CH₂C≡CH —CF₂H —CH₃ Hcycloheptyl 2.022 —CH₂C≡CH —CF₂H —CH₃ H

2.023 —CH₂C≡CH —CF₃ —CH₂OCH₃ H 4-F-phenyl 2.024 —CH₂C≡CH —CF₃ —CH₂OCH₃ H4-Cl-phenyl 2.025 —CH₂C≡CH —CF₃ —CH₂OCH₃ H 3-Me-cyclopentyl 2.026—CH₂C≡CH —CF₃ —CH₂OCH₃ H 3-Me-cyclohexyl 2.027 —CH₂C≡CH —CF₃ —CH₂OCH₃ Hcycloheptyl 2.028 —CH₂C≡CH —CF₃ —CH₂OCH₃ H

2.029 —CH₂C≡CH —CF₃ —CH₃ F 4-F-phenyl 2.030 —CH₂C≡CH —CF₃ —CH₃ F4-Cl-phenyl 2.031 —CH₂C≡CH —CF₃ —CH₃ F 3-Me-cyclopentyl 2.032 —CH₂C≡CH—CF₃ —CH₃ F 3-Me-cyclohexyl 2.033 —CH₂C≡CH —CF₃ —CH₃ F cycloheptyl 2.034—CH₂C≡CH —CF₃ —CH₃ F

2.035 —COCH₃ —CF₃ —CH₃ H 4-F-phenyl 2.036 —COCH₃ —CF₃ —CH₃ H 4-Cl-phenyl2.037 —COCH₃ —CF₃ —CH₃ H 4-Br-phenyl 2.038 —COCH₃ —CF₃ —CH₃ H3-Me-cyclopentyl 2.039 —COCH₃ —CF₃ —CH₃ H 4-Me-cyclohexyl 2.040 —COCH₃—CF₃ —CH₃ H 3-Me-cyclohexyl 2.041 —COCH₃ —CF₃ —CH₃ H cycloheptyl 2.042—COCH₃ —CF₃ —CH₃ H

 95-97 2.043 —COCH₃ —CF₂H —CH₃ H 4-F-phenyl 2.044 —COCH₃ —CF₂H —CH₃ H4-Cl-phenyl 2.045 —COCH₃ —CF₂H —CH₃ H 3-Me-cyclopentyl 2.046 —COCH₃—CF₂H —CH₃ H 3-Me-cyclohexyl 2.047 —COCH₃ —CF₂H —CH₃ H cycloheptyl 2.048—COCH₃ —CF₂H —CH₃ H

2.049 —COCH₃ —CF₃ —CH₂OCH₃ H 4-F-phenyl 2.050 —COCH₃ —CF₃ —CH₂OCH₃ H4-Cl-phenyl 2.051 —COCH₃ —CF₃ —CH₂OCH₃ H 3-Me-cyclopentyl 2.052 —COCH₃—CF₃ —CH₂OCH₃ H 3-Me-cyclohexyl 2.053 —COCH₃ —CF₃ —CH₂OCH₃ H cycloheptyl2.054 —COCH₃ —CF₃ —CH₂OCH₃ H

2.055 —COCH₃ —CF₃ —CH₃ F 4-F-phenyl 2.056 —COCH₃ —CF₃ —CH₃ F 4-Cl-phenylresin; M⁺ = 421(³⁵Cl) 2.057 —COCH₃ —CF₃ —CH₃ F 4-Br-phenyl 2.058 —COCH₃—CF₃ —CH₃ F 3-Me-cyclohexyl 2.059 —COCH₃ —CF₃ —CH₃ F cycloheptyl 2.060—COCH₃ —CF₃ —CH₃ F

2.061 —COCH₂CH₃ —CF₃ —CH₃ H 4-F-phenyl 2.062 —COCH₂CH₃ —CF₃ —CH₃ H4-Cl-phenyl resin; M⁺ = 435(³⁵Cl) 2.063 —COCH₂CH₃ —CF₃ —CH₃ H4-Br-phenyl 2.064 —COCH₂CH₃ —CF₃ —CH₃ H 3-Me-cyclopentyl 2.065 —COCH₂CH₃—CF₃ —CH₃ H 4-Me-cyclohexyl 2.066 —COCH₂CH₃ —CF₃ —CH₃ H 3-Me-cyclohexyl2.067 —COCH₂CH₃ —CF₃ —CH₃ H cycloheptyl 2.068 —COCH₂CH₃ —CF₃ —CH₃ H

 92-94 2.069 —COCH₂CH₃ —CF₃ —CH₃ H 4-F-phenyl 2.070 —COCH₂CH₃ —CF₂H —CH₃H 4-Cl-phenyl 2.071 —COCH₂CH₃ —CF₂H —CH₃ H 4-Br-phenyl 2.072 —COCH₂CH₃—CF₂H —CH₃ H cycloheptyl 2.073 —COCH₂CH₃ —CF₂H —CH₃ H

2.074 —COCH₂CH₂CH₃ —CF₃ —CH₃ H 4-F-phenyl 2.075 —COCH₂CH₂CH₃ —CF₃ —CH₃ H4-Cl-phenyl resin; M⁺ = 2.076 —COCH₂CH₂CH₃ —CF₃ —CH₃ H 4-Br-phenyl 2.077—COCH₂CH₂CH₃ —CF₃ —CH₃ H cycloheptyl 2.078 —COCH₂CH₂CH₃ —CF₃ —CH₃ H

2.079 —COcyclopropyl —CF₃ —CH₃ H 4-F-phenyl 2.080 —COcyclopropyl —CF₃—CH₃ H 4-Cl-phenyl 2.081 —COcyclopropyl —CF₃ —CH₃ H 4-Br-phenyl 2.082—COcyclopropyl —CF₃ —CH₃ H cycloheptyl 2.083 —COcyclopropyl —CF₃ —CH₃ H

2.084 —COCH₂OCH₃ —CF₃ —CH₃ H 4-F-phenyl 2.085 —COCH₂OCH₃ —CF₃ —CH₃ H4-Cl-phenyl  55-57 2.086 —COCH₂OCH₃ —CF₃ —CH₃ H 4-Br-phenyl 2.087—COCH₂OCH₃ —CF₃ —CH₃ H 3-Me-cyclopentyl 2.088 —COCH₂OCH₃ —CF₃ —CH₃ H4-Me-cyclohexyl 2.089 —COCH₂OCH₃ —CF₃ —CH₃ H 3-Me-cyclohexyl 2.090—COCH₂OCH₃ —CF₃ —CH₃ H cycloheptyl 2.091 —COCH₂OCH₃ —CF₃ —CH₃ H

resin;M⁺ = 425 2.092 —COCH₂OCH₃ —CF₂H —CH₃ H 4-F-phenyl 2.093 —COCH₂OCH₃—CF₂H —CH₃ H 4-F-phenyl 2.094 —COCH₂OCH₃ —CF₂H —CH₃ H 4-Cl-phenyl 2.095—COCH₂OCH₃ —CF₂H —CH₃ H 4-Br-phenyl 2.096 —COCH₂OCH₃ —CF₂H —CH₃ Hcycloheptyl 2.097 —COCH₂OCH₃ —CF₂H —CH₃ H

2.098 —COCH₂OCH₃ —CF₃ —CH₃ F 4-Cl-phenyl 2.099 —COCH₂OCH₂CH₃ —CF₃ —CH₃ H4-F-phenyl 2.100 —COCH₂OCH₂CH₃ —CF₃ —CH₃ H 4-Cl-phenyl 2.101—COCH₂OCH₂CH₃ —CF₃ —CH₃ H 4-Br-phenyl 2.102 —COCH₂OCH₂CH₃ —CF₃ —CH₃ H3-Me-cyclohexyl 2.103 —COCH₂OCH₂CH₃ —CF₃ —CH₃ H cycloheptyl 2.104—COCH₂OCH₂CH₃ —CF₃ —CH₃ H

2.105 —COOCH₃ —CF₃ —CH₃ H 4-F-phenyl 2.106 —COOCH₃ —CF₃ —CH₃ H4-Cl-phenyl 2.107 —COOCH₃ —CF₃ —CH₃ H 4-Br-phenyl 2.108 —COOCH₃ —CF₃—CH₃ H 3-Me-cyclopentyl 2.109 —COOCH₃ —CF₃ —CH₃ H 4-Me-cyclohexyl 2.110—COOCH₃ —CF₃ —CH₃ H 3-Me-cyclohexyl 2.111 —COOCH₃ —CF₃ —CH₃ Hcycloheptyl 2.112 —COOCH₃ —CF₃ —CH₃ H

2.113 —COOCH₃ —CF₂H —CH₃ H 4-F-phenyl 2.114 —COOCH₃ —CF₂H —CH₃ H4-Cl-phenyl 2.115 —COOCH₃ —CF₂H —CH₃ H 4-Br-phenyl 2.116 —COOCH₃ —CF₂H—CH₃ H cycloheptyl 2.117 —COOCH₃ —CF₂H —CH₃ H

2.118 —COOCH₃ —CF₃ —CH₃ F 4-F-phenyl 2.119 —COOCH₃ —CF₃ —CH₃ F4-Cl-phenyl 2.120 —COOCH₃ —CF₃ —CH₃ F cycloheptyl 2.121 —CH═C═CH₂ —CF₃—CH₃ H 4-F-phenyl 2.122 —CH═C═CH₂ —CF₃ —CH₃ H 4-Cl-phenyl 144-146 2.123—CH═C═CH₂ —CF₃ —CH₃ H 4-Br-phenyl 146-149 2.124 —CH═C═CH₂ —CF₂H —CH₃ H4-F-phenyl 148-149 2.125 —CH═C═CH₂ —CF₂H —CH₃ H 4-Cl-phenyl 157-1592.126 —CH═C═CH₂ —CF₂H —CH₃ H 4-Br-phenyl 163-164

TABLE 3 Pyrrolecarboxamides (Ib)

Cmpd. phys. data no. R₁ R₄ R₅ R₆ Z m.p. ° C. 3.01 —CH₂CH═CH₂ —CF₃ —CH₃ H4-F-phenyl resin; M⁺ = 402 3.02 —CH₂CH═CH₂ —CF₃ —CH₃ H 4-Br-phenyl 3.03—CH₂CH═CH₂ —CF₃ —CH₃ H 3-Me-cyclopentyl 3.04 —CH₂CH═CH₂ —CF₃ —CH₃ H4-Me-cyclohexyl 3.05 —CH₂CH═CH₂ —CF₃ —CH₃ H 3-Me-cyclohexyl 3.06—CH₂CH═CH₂ —CF₃ —CH₃ H cycloheptyl 3.07 —CH₂CH═CH₂ —CF₃ —CH₃ H

3.08 —CH₂C≡CH —CF₃ —CH₃ H 4-F-phenyl 109-112 3.09 —CH₂C≡CH —CF₃ —CH₃ H4-Cl-phenyl 3.10 —CH₂C≡CH —CF₃ —CH₃ H 4-Br-phenyl 130-131 3.11 —CH₂C≡CH—CF₃ —CH₃ H 3-Me-cyclopentyl 3.12 —CH₂C≡CH —CF₃ —CH₃ H 4-Me-cyclohexyl3.13 —CH₂C≡CH —CF₃ —CH₃ H 3-Me-cyclohexyl 3.14 —CH₂C≡CH —CF₃ —CH₃ Hcycloheptyl 3.15 —CH₂C≡CH —CF₃ —CH₃ H

3.16 —CH₂C≡CH —CF₃ —CH₂OCH₃ H 4-F-phenyl 3.17 —CH₂C≡CH —CF₃ —CH₂OCH₃ H4-Cl-phenyl 3.18 —CH₂C≡CH —CF₃ —CH₂OCH₃ H 3-Me-cyclopentyl 3.19 —CH₂C≡CH—CF₃ —CH₂OCH₃ H 3-Me-cyclohexyl 3.20 —CH₂C≡CH —CF₃ —CH₂OCH₃ Hcycloheptyl 3.21 —CH₂C≡CH —CF₃ —CH₂OCH₃ H

3.22 —CH₂C≡CH —CF₃ —CH₃ F 4-F-phenyl 3.23 —CH₂C≡CH —CF₃ —CH₃ F4-Cl-phenyl 3.24 —CH₂C≡CH —CF₃ —CH₃ F 3-Me-cyclopentyl 3.25 —CH₂C≡CH—CF₃ —CH₃ F 3-Me-cyclohexyl 3.26 —CH₂C≡CH —CF₃ —CH₃ F cycloheptyl 3.27—CH₂C≡CH —CF₃ —CH₃ F

3.28 —COCH₃ —CF₃ —CH₃ H 4-F-phenyl resin; M⁺ = 404 3.29 —COCH₃ —CF₃ —CH₃H 4-Cl-phenyl 3.30 —COCH₃ —CF₃ —CH₃ H 4-Br-phenyl 3.31 —COCH₃ —CF₃ —CH₃H 3-Me-cyclopentyl 3.32 —COCH₃ —CF₃ —CH₃ H 4-Me-cyclohexyl 3.33 —COCH₃—CF₃ —CH₃ H 3-Me-cyclohexyl 3.34 —COCH₃ —CF₃ —CH₃ H cycloheptyl 3.35—COCH₃ —CF₃ —CH₃ H

3.36 —COCH₃ —CF₃ —CH₂OCH₃ H 4-F-phenyl 3.37 —COCH₃ —CF₃ —CH₂OCH₃ H4-Cl-phenyl 3.38 —COCH₃ —CF₃ —CH₂OCH₃ H 3-Me-cyclopentyl 3.39 —COCH₃—CF₃ —CH₂OCH₃ H 3-Me-cyclohexyl 3.40 —COCH₃ —CF₃ —CH₂OCH₃ H cycloheptyl3.41 —COCH₃ —CF₃ —CH₂OCH₃ H

3.42 —COCH₃ —CF₃ —CH₃ F 4-F-phenyl 3.43 —COCH₃ —CF₃ —CH₃ F 4-Cl-phenyl3.44 —COCH₃ —CF₃ —CH₃ F 3-Me-cyclopentyl 3.45 —COCH₃ —CF₃ —CH₃ F3-Me-cyclohexyl 3.46 —COCH₃ —CF₃ —CH₃ F cycloheptyl 3.47 —COCH₃ —CF₃—CH₃ F

3.48 —COCH₂CH₃ —CF₃ —CH₃ H 4-F-phenyl 3.49 —COCH₂CH₃ —CF₃ —CH₃ H4-Cl-phenyl 3.50 —COCH₂CH₃ —CF₃ —CH₃ H 4-Br-phenyl 3.51 —COCH₂CH₃ —CF₃—CH₃ H 3-Me-cyclopentyl 3.52 —COCH₂CH₃ —CF₃ —CH₃ H 4-Me-cyclohexyl 3.53—COCH₂CH₃ —CF₃ —CH₃ H 3-Me-cyclohexyl 3.54 —COCH₂CH₃ —CF₃ —CH₃ Hcycloheptyl 3.55 —COCH₂CH₃ —CF₃ —CH₃ H

3.56 —COCH₂CH₃ —CF₃ —CH₃ H 4-F-phenyl 3.57 —COCH₂CH₂CH₃ —CF₃ —CH₃ H4-F-phenyl 3.58 —COCH₂CH₂CH₃ —CF₃ —CH₃ H 4-Cl-phenyl 3.59 —COCH₂CH₂CH₃—CF₃ —CH₃ H 4-Br-phenyl 3.60 —COCH₂CH₂CH₃ —CF₃ —CH₃ H cycloheptyl 3.61—COCH₂CH₂CH₃ —CF₃ —CH₃ H

resin;M⁺ = 422 3.62 —COcyclopropyl —CF₃ —CH₃ H 4-F-phenyl 3.63—COcyclopropyl —CF₃ —CH₃ H 4-Cl-phenyl 3.64 —COcyclopropyl —CF₃ —CH₃ H4-Br-phenyl 3.65 —COcyclopropyl —CF₃ —CH₃ H cycloheptyl 3.66—COcyclopropyl —CF₃ —CH₃ H

3.67 —COCH₂OCH₃ —CF₃ —CH₃ H 4-F-phenyl resin; M⁺ = 434 3.68 —COCH₂OCH₃—CF₃ —CH₃ H 4-Cl-phenyl 3.69 —COCH₂OCH₃ —CF₃ —CH₃ H 4-Br-phenyl 3.70—COCH₂OCH₃ —CF₃ —CH₃ H 3-Me-cyclopentyl 3.71 —COCH₂OCH₃ —CF₃ —CH₃ H4-Me-cyclohexyl 3.72 —COCH₂OCH₃ —CF₃ —CH₃ H 3-Me-cyclohexyl 3.73—COCH₂OCH₃ —CF₃ —CH₃ H cycloheptyl 3.74 —COCH₂OCH₃ —CF₃ —CH₃ H

3.75 —COCH₂OCH₃ —CF₃ —CH₃ F 4-Cl-phenyl 3.76 —COCH₂OCH₂CH₃ —CF₃ —CH₃ H4-F-phenyl 3.77 —COCH₂OCH₂CH₃ —CF₃ —CH₃ H 4-Cl-phenyl 3.78 —COCH₂OCH₂CH₃—CF₃ —CH₃ H 4-Br-phenyl 3.79 —COCH₂OCH₂CH₃ —CF₃ —CH₃ H 3-Me-cyclohexyl3.80 —COCH₂OCH₂CH₃ —CF₃ —CH₃ H cycloheptyl 3.81 —COCH₂OCH₂CH₃ —CF₃ —CH₃H

3.82 —COOCH₃ —CF₃ —CH₃ H 4-F-phenyl 3.83 —COOCH₃ —CF₃ —CH₃ H 4-Cl-phenyl3.84 —COOCH₃ —CF₃ —CH₃ H 4-Br-phenyl 3.85 —COOCH₃ —CF₃ —CH₃ H3-Me-cyclopentyl 3.86 —COOCH₃ —CF₃ —CH₃ H 4-Me-cyclohexyl 3.87 —COOCH₃—CF₃ —CH₃ H 3-Me-cyclohexyl 3.88 —COOCH₃ —CF₃ —CH₃ H cycloheptyl 3.89—COOCH₃ —CF₃ —CH₃ H

3.90 —COOCH₃ —CF₃ —CH₃ F 4-F-phenyl 3.91 —COOCH₃ —CF₃ —CH₃ F 4-Cl-phenyl3.92 —COOCH₃ —CF₃ —CH₃ F cycloheptyl 3.93 —CH═C═CH₂ —CF₃ —CH₃ H4-F-phenyl 3.94 —CH═C═CH₂ —CF₃ —CH₃ H 4-Cl-phenyl 3.95 —CH═C═CH₂ —CF₃—CH₃ H 4-Bromophenyl 162-163

TABLE 4 Thiazolecarboxamides (Ic)

Cmpd. phys. data no. R₁ R₄ R₅ Z m.p. ° C. 4.01 —CH₂CH═CH₂ —CF₃ —CH₃4-Cl-phenyl 4.02 —CH₂CH═CH₂ —CF₃ —CH₃ 4-Br-phenyl 4.03 —CH₂CH═CH₂ —CF₃—CH₃ 4-Me-cyclohexyl 4.04 —CH₂CH═CH₂ —CF₃ —CH₃ 3-Me-cyclohexyl 4.05—CH₂CH═CH₂ —CF₃ —CH₃ cycloheptyl 4.06 —CH₂CH═CH₂ —CF₃ —CH₃

4.07 —CH₂C≡CH —CF₃ —CH₃ 4-F-phenyl 4.08 —CH₂C≡CH —CF₃ —CH₃ 4-Cl-phenyl4.09 —CH₂C≡CH —CF₃ —CH₃ 4-Br-phenyl 4.10 —CH₂C≡CH —CF₃ —CH₃3-Me-cyclopentyl 4.11 —CH₂C≡CH —CF₃ —CH₃ 4-Me-cyclohexyl 4.12 —CH₂C≡CH—CF₃ —CH₃ 3-Me-cyclohexyl 4.13 —CH₂C≡CH —CF₃ —CH₃ cycloheptyl 4.14—CH₂C≡CH —CF₃ —CH₃

4.15 —CH₂C≡CH —CF₃ —CH₂OCH₃ 4-F-phenyl 4.16 —CH₂C≡CH —CF₃ —CH₂OCH₃4-Cl-phenyl 4.17 —CH₂C≡CH —CF₃ —CH₂OCH₃ cycloheptyl 4.18 —CH₂C≡CH —CF₃—CH₂OCH₃

4.19 —COCH₃ —CF₃ —CH₃ 4-Cl-phenyl 4.20 —COCH₃ —CF₃ —CH₃ 4-Br-phenyl 4.21—COCH₃ —CF₃ —CH₃ 3-Me-cyclopentyl 4.22 —COCH₃ —CF₃ —CH₃ 4-Me-cyclohexyl4.23 —COCH₃ —CF₃ —CH₃ 3-Me-cyclohexyl 4.24 —COCH₃ —CF₃ —CH₃ cycloheptyl4.25 —COCH₃ —CF₃ —CH₃

4.26 —COCH₂CH₃ —CF₃ —CH₃ 4-F-phenyl 4.27 —COCH₂CH₃ —CF₃ —CH₃ 4-Cl-phenyl4.28 —COCH₂CH₃ —CF₃ —CH₃ 4-Br-phenyl 4.29 —COCH₂CH₃ —CF₃ —CH₃cycloheptyl 4.30 —COCH₂CH₃ —CF₃ —CH₃

4.31 —COCH₂OCH₃ —CF₃ —CH₃ 4-Cl-phenyl 4.32 —COCH₂OCH₃ —CF₃ —CH₃4-Br-phenyl 4.33 —COCH₂OCH₃ —CF₃ —CH₃ 3-Me-cyclopentyl 4.34 —COCH₂OCH₃—CF₃ —CH₃ 4-Me-cyclohexyl 4.35 —COCH₂OCH₃ —CF₃ —CH₃ 3-Me-cyclohexyl 4.36—COCH₂OCH₃ —CF₃ —CH₃ cycloheptyl 4.37 —COCH₂OCH₃ —CF₃ —CH₃

4.38 —COCH₂OCH₂CH₃ —CF₃ —CH₃ 4-F-phenyl 4.39 —COCH₂OCH₂CH₃ —CF₃ —CH₃4-Cl-phenyl 4.40 —COCH₂OCH₂CH₃ —CF₃ —CH₃ cycloheptyl 4.41 —COCH₂OCH₂CH₃—CF₃ —CH₃

4.42 —COOCH₃ —CF₃ —CH₃ 4-F-phenyl resin 4.43 —COOCH₃ —CF₃ —CH₃4-Cl-phenyl 4.44 —COOCH₃ —CF₃ —CH₃ 4-Br-phenyl 4.45 —COOCH₃ —CF₃ —CH₃cycloheptyl 4.46 —COOCH₃ —CF₃ —CH₃

TABLE 5 Oxazolecarboxamides (Id)

Cmpd. phys. data no. R₁ R₄ R₅ Z m.p. ° C. 5.01 —CH₂CH═CH₂ —CF₃ —CH₃4-Cl-phenyl 5.02 —CH₂CH═CH₂ —CF₃ —CH₃ 4-Br-phenyl 5.03 —CH₂CH═CH₂ —CF₃—CH₃ 4-Me-cyclohexyl 5.04 —CH₂CH═CH₂ —CF₃ —CH₃ 3-Me-cyclohexyl 5.05—CH₂CH═CH₂ —CF₃ —CH₃ cycloheptyl 5.06 —CH₂CH═CH₂ —CF₃ —CH₃

5.07 —CH₂C≡CH —CF₃ —CH₃ 4-F-phenyl 5.08 —CH₂C≡CH —CF₃ —CH₃ 4-Cl-phenyl5.09 —CH₂C≡CH —CF₃ —CH₃ 4-Br-phenyl 5.10 —CH₂C≡CH —CF₃ —CH₃3-Me-cyclopentyl 5.11 —CH₂C≡CH —CF₃ —CH₃ 4-Me-cyclohexyl 5.12 —CH₂C≡CH—CF₃ —CH₃ 3-Me-cyclohexyl 5.13 —CH₂C≡CH —CF₃ —CH₃ cycloheptyl 5.14—CH₂C≡CH —CF₃ —CH₃

5.15 —CH₂C≡CH —CF₃ —CH₂OCH₃ 4-F-phenyl 5.16 —CH₂C≡CH —CF₃ —CH₂OCH₃4-Cl-phenyl 5.17 —CH₂C≡CH —CF₃ —CH₂OCH₃ cycloheptyl 5.18 —CH₂C≡CH —CF₃—CH₂OCH₃

5.19 —COCH₃ —CF₃ —CH₃ 4-Cl-phenyl 5.20 —COCH₃ —CF₃ —CH₃ 4-Br-phenyl 5.21—COCH₃ —CF₃ —CH₃ 3-Me-cyclopentyl 5.22 —COCH₃ —CF₃ —CH₃ 4-Me-cyclohexyl5.23 —COCH₃ —CF₃ —CH₃ 3-Me-cyclohexyl 5.24 —COCH₃ —CF₃ —CH₃ cycloheptyl5.25 —COCH₃ —CF₃ —CH₃

5.26 —COCH₂CH₃ —CF₃ —CH₃ 4-F-phenyl 5.27 —COCH₂CH₃ —CF₃ —CH₃ 4-Cl-phenyl5.28 —COCH₂CH₃ —CF₃ —CH₃ 4-Br-phenyl 5.29 —COCH₂CH₃ —CF₃ —CH₃cycloheptyl 5.30 —COCH₂CH₃ —CF₃ —CH₃

5.31 —COCH₂OCH₃ —CF₃ —CH₃ 4-F-phenyl 5.32 —COCH₂OCH₃ —CF₃ —CH₃4-Cl-phenyl 5.33 —COCH₂OCH₃ —CF₃ —CH₃ 3-Me-cyclopentyl 5.34 —COCH₂OCH₃—CF₃ —CH₃ 4-Me-cyclohexyl 5.35 —COCH₂OCH₃ —CF₃ —CH₃ 3-Me-cyclohexyl 5.36—COCH₂OCH₃ —CF₃ —CH₃ cycloheptyl 5.37 —COCH₂OCH₃ —CF₃ —CH₃

5.38 —COCH₂OCH₂CH₃ —CF₃ —CH₃ 4-F-phenyl 5.39 —COCH₂OCH₂CH₃ —CF₃ —CH₃4-Cl-phenyl 5.40 —COCH₂OCH₂CH₃ —CF₃ —CH₃ cycloheptyl 5.41 —COCH₂OCH₂CH₃—CF₃ —CH₃

5.42 —COOCH₃ —CF₃ —CH₃ 4-F-phenyl 5.43 —COOCH₃ —CF₃ —CH₃ 4-Cl-phenyl5.44 —COOCH₃ —CF₃ —CH₃ 4-Br-phenyl 5.45 —COOCH₃ —CF₃ —CH₃ cycloheptyl5.46 —COOCH₃ —CF₃ —CH₃

TABLE 6 Pyridine carboxylic acid amides (Ie)

phys. data Cmpd. m.p. no. R₁ R₄ Z ° C. 6.01 —CH₂CH═CH₂ —Cl 4-F-phenyl6.02 —CH₂CH═CH₂ —Cl 4-Cl-phenyl 6.03 —CH₂CH═CH₂ —Cl 4-Br-phenyl 6.04—CH₂CH═CH₂ —Cl cycloheptyl 6.05 —CH₂CH═CH₂ —Cl

6.06 —CH₂C≡CH —CF₃ 4-F-phenyl 6.07 —CH₂C≡CH —CF₃ 4-Cl-phenyl 6.08—CH₂C≡CH —CF₃ 4-Br-phenyl 6.09 —CH₂C≡CH —CF₃ cycloheptyl 6.10 —CH₂C≡CH—CF₃

6.11 —CH₂C≡CH —Cl 4-F-phenyl 6.12 —CH₂C≡CH —Cl 4-Cl-phenyl 6.13 —CH₂C≡CH—Cl 4-Br-phenyl 6.14 —CH₂C≡CH —Cl cycloheptyl 6.15 —CH₂C≡CH —Cl

6.16 —CH₂C≡CH —CF₃ 4-F-phenyl 6.17 —CH₂C≡CH —CF₃ 4-Cl-phenyl 6.18—CH₂C≡CH —CF₃ 4-Br-phenyl 6.19 —CH₂C≡CH —CF₃ cycloheptyl 6.20 —CH₂C≡CH—CF₃

6.21 —COCH₃ —Cl 4-F-phenyl 6.22 —COCH₃ —Cl 4-Cl-phenyl 6.23 —COCH₃ —Cl4-Br-phenyl 6.24 —COCH₃ —Cl 4-Me-cyclohexyl 6.25 —COCH₃ —Cl3-Me-cyclohexyl 6.26 —COCH₃ —Cl cycloheptyl 6.27 —COCH₃ —Cl

6.28 —COCH₃ —CF₃ 4-F-phenyl 6.29 —COCH₃ —CF₃ 4-Cl-phenyl 6.30 —COCH₃—CF₃ 4-Br-phenyl 6.31 —COCH₃ —CF₃ 4-Me-cyclohexyl 6.32 —COCH₃ —CF₃3-Me-cyclohexyl 6.33 —COCH₃ —CF₃ cycloheptyl 6.34 —COCH₃ —CF₃

6.35 —COCH₂CH₃ —Cl 4-F-phenyl 6.36 —COCH₂CH₃ —Cl 4-Cl-phenyl 6.37—COCH₂CH₃ —Cl 4-Br-phenyl 6.38 —COCH₂CH₃ —Cl 3-Me-cyclohexyl 6.39—COCH₂CH₃ —Cl cycloheptyl 6.40 —COCH₂CH₃ —Cl

6.41 —COCH₂CH₃ —CF₃ 4-F-phenyl 6.42 —COCH₂CH₃ —CF₃ 4-Cl-phenyl 6.43—COCH₂CH₃ —CF₃ 4-Br-phenyl 6.44 —COCH₂CH₃ —CF₃ cycloheptyl 6.45—COCH₂CH₃ —CF₃

6.46 —COCH₂OCH₃ —Cl 4-F-phenyl 6.47 —COCH₂OCH₃ —Cl 4-Cl-phenyl 6.48—COCH₂OCH₃ —Cl 4-Br-phenyl 6.49 —COCH₂OCH₃ —Cl cycloheptyl 6.50—COCH₂OCH₃ —Cl

6.51 —COCH₂OCH₃ —CF₃ 4-F-phenyl 6.52 —COCH₂OCH₃ —CF₃ 4-Cl-phenyl 6.53—COCH₂OCH₃ —CF₃ 4-Br-phenyl 6.54 —COCH₂OCH₃ —CF₃ cycloheptyl 6.55—COCH₂OCH₃ —CF₃

6.56 —COCH₂OCH₂CH₃ —Cl 4-F-phenyl 6.57 —COCH₂OCH₂CH₃ —Cl 4-Cl-phenyl6.58 —COCH₂OCH₂CH₃ —Cl cycloheptyl 6.59 —COCH₂OCH₂CH₃ —Cl

6.60 —COCH₂OCH₂CH₃ —CF₃ 4-F-phenyl 6.61 —COCH₂OCH₂CH₃ —CF₃ 4-Cl-phenyl6.62 —COCH₂OCH₂CH₃ —CF₃ cycloheptyl 6.63 —COCH₂OCH₂CH₃ —CF₃

6.64 —COOCH₃ —Cl 4-F-phenyl 6.65 —COOCH₃ —Cl 4-Cl-phenyl 6.66 —COOCH₃—Cl 4-Br-phenyl 6.67 —COOCH₃ —Cl cycloheptyl 6.68 —COOCH₃ —Cl

6.69 —COOCH₃ —CF₃ 4-F-phenyl 6.70 —COOCH₃ —CF₃ 4-Cl-phenyl 6.71 —COOCH₃—CF₃ 4-Br-phenyl 6.72 —COOCH₃ —CF₃ cycloheptyl 6.73 —COOCH₃ —CF₃

TABLE 7 Compounds of the general formula If (If)

Cmpd. phys. data no. R₁ R₄ R₅ R₆ m.p. ° C. 7.01 —CH₂CH═CH₂ —CF₃ —CH₃ H7.02 —CH₂CH═CH₂ —CF₃ —CH₃ F 7.03 —CH₂CH═CH₂ —CF₂H —CH₃ H 7.04 —CH₂C≡CH—CF₃ —CH₃ H 7.05 —CH₂C≡CH —CF₃ —CH₃ F 7.06 —CH₂C≡CH —CF₂H —CH₃ H 7.07—COCH₃ —CF₃ —CH₃ H 7.08 —COCH₃ —CF₂H —CH₃ H 7.09 —COCH₂CH₃ —CF₃ —CH₃ H7.10 —COCH₂CH₃ —CF₂H —CH₃ H 7.11 —COCH₂OCH₃ —CF₃ —CH₃ H 7.12 —COCH₂OCH₃—CF₂H —CH₃ H 7.13 —COCH₂OCH₃ —CF₃ —CH₃ F 7.14 —COCH₂OCH₂CH₃ —CF₃ —CH₃ H7.15 —COCH₂OCH₂CH₃ —CF₂H —CH₃ H 7.16 —COCH₂OCH₂CH₃ —CF₃ —CH₃ F 7.17—COOCH₃ —CF₃ —CH₃ H 7.18 —COOCH₃ —CF₂H —CH₃ H 7.19 —COOCH₃ —CF₃ —CH₃ F7.20 —COOCH₃ —CF₂H —CH₃ F

TABLE 8 Compounds of the general formula Ig (Ig)

Cmpd. phys. data no. R₁ R₄ R₅ R₆ m.p. ° C. 8.01 —CH₂CH═CH₂ —CF₃ —CH₃ H8.02 —CH₂CH═CH₂ —CF₃ —CH₂OCH₃ H 8.03 —CH₂C≡CH —CF₃ —CH₃ H resin 8.04—CH₂C≡CH —CF₃ —CH₂OCH₃ H 8.05 —CH₂C≡CH —CF₃ —CH₃ F 8.06 —COCH₃ —CF₃ —CH₃H 8.07 —COCH₃ —CF₃ —CH₂OCH₃ H 8.08 —COCH₂CH₃ —CF₃ —CH₃ H 8.09 —COCH₂CH₃—CF₃ —CH₂OCH₃ H 8.10 —COCH₂OCH₃ —CF₃ —CH₃ H 8.11 —COCH₂OCH₃ —CF₃ —CH₃ F8.12 —COCH₂OCH₃ —CF₃ —CH₂OCH₃ H 8.13 —COCH₂OCH₂CH₃ —CF₃ —CH₃ H 8.14—COCH₂OCH₂CH₃ —CF₃ —CH₂OCH₃ H 8.15 —COOCH₃ —CF₃ —CH₃ H 8.16 —COOCH₃ —CF₃—CH₂OCH₃ H 8.17 —COOCH₃ —CF₃ —CH₃ F

TABLE 9 Compounds of the general formula Ih (Ih)

Cmpd. phys. data no. R₁ R₄ R₅ R₆ m.p. ° C. 9.01 —CH₂CH═CH₂ —CF₃ —CH₃ H9.02 —CH₂CH═CH₂ —CF₃ —CH₃ F 9.03 —CH₂CH═CH₂ —CF₂H —CH₃ H 9.04 —CH₂C≡CH—CF₃ —CH₃ H resin 9.05 —CH₂C≡CH —CF₃ —CH₃ F 9.06 —CH₂C≡CH —CF₂H —CH₃ H9.07 —COCH₃ —CF₃ —CH₃ H 9.08 —COCH₃ —CF₂H —CH₃ H 9.09 —COCH₂CH₃ —CF₃—CH₃ H 9.10 —COCH₂CH₃ —CF₂H —CH₃ H 9.11 —COCH₂OCH₃ —CF₃ —CH₃ H 9.12—COCH₂OCH₃ —CF₂H —CH₃ H 9.13 —COCH₂OCH₃ —CF₃ —CH₃ F 9.14 —COCH₂OCH₂CH₃—CF₃ —CH₃ H 9.15 —COCH₂OCH₂CH₃ —CF₂H —CH₃ H 9.18 —COOCH₃ —CF₂H —CH₃ H9.19 —COOCH₃ —CF₃ —CH₃ F 9.20 —COOCH₃ —CF₂H —CH₃ F

TABLE 10 Compounds of the general formula Ii (Ii)

Cmpd. phys. data no. R₁ R₄ R₅ R₆ m.p. ° C. 10.01 —CH₂CH═CH₂ —CF₃ —CH₃ H10.02 —CH₂CH═CH₂ —CF₃ —CH₂OCH₃ H 10.03 —CH₂C≡CH —CF₃ —CH₃ H 142-14410.04 —CH₂C≡CH —CF₃ —CH₂OCH₃ H 10.05 —CH₂C≡CH —CF₃ —CH₃ F 10.06 —COCH₃—CF₃ —CH₃ H 10.07 —COCH₃ —CF₃ —CH₂OCH₃ H 10.08 —COCH₂CH₃ —CF₃ —CH₃ H10.09 —COCH₂CH₃ —CF₃ —CH₂OCH₃ H 10.10 —COCH₂OCH₃ —CF₃ —CH₃ H oil; M⁺ =422 10.11 —COCH₂OCH₃ —CF₃ —CH₃ F 10.12 —COCH₂OCH₃ —CF₃ —CH₂OCH₃ H 10.13—COCH₂OCH₂CH₃ —CF₃ —CH₃ H 10.14 —COCH₂OCH₂CH₃ —CF₃ —CH₂OCH₃ H 10.15—COOCH₃ —CF₃ —CH₃ H 10.16 —COOCH₃ —CF₃ —CH₂OCH₃ H 10.17 —COOCH₃ —CF₃—CH₃ F

FORMULATION EXAMPLES FOR COMPOUNDS OF FORMULA I

Working procedures for preparing formulations of the compounds offormula I such as Emulsifiable concentrates, Solutions, Granulates,Dusts and Wettable powders are described in WO 97/33890.

BIOLOGICAL EXAMPLES Fungicidal Actions Example B-1 Action AgainstPuccinia recondita /Wheat (Brownrust on Wheat)

1 week old wheat plants cv. Arina are treated with the formulated testcompound (0.02% active ingredient) in a spray chamber. One day afterapplication wheat plants are inoculated by spraying a spore suspension(1×10⁵ uredospores/ml) on the test plants. After an incubation period of2 days at 20° C. and 95% r. h. plants are kept in a greenhouse for 8days at 20° C. and 60% r.h. The disease incidence is assessed 10 daysafter inoculation.

Compounds of Tables 1 to 10 show good activity in these tests. Thecompounds 1.24, 1.50, 2.1, 2.7, 2.9, 2.15, 2.42, 2.56, 2.62, 2.68, 2.75,2.85, 2.91, 3.1, 3.8, 3.28, 3.67, 3.74, 10.3 and 10.10 exhibit strongefficacy (<20% infestation).

Example B-2 Action Against Podosphaera leucotricha /Apple (PowderyMildew on Apple)

5 week old apple seedlings cv. McIntosh are treated with the formulatedtest compound (0.002% active ingredient) in a spray chamber. One dayafter application apple plants are inoculated by shaking plants infectedwith apple powdery mildew above the test plants. After an incubationperiod of 12 days at 22° C. and 60% r. h. under a light regime of 14/10h (light/dark) the disease incidence is assessed.

Compounds of Tables 1 to 10 show good activity in this test. Thecompounds 1.24, 1.50, 2.1, 2.7, 2.9, 2.15, 2.42, 2.56, 2.62, 2.68, 2.75,2.85, 2.91, 3.1, 3.8, 3.28, 3.67, 3.74, 10.3 and 10.10 exhibit strongefficacy (<20% infestation).

Example B-3 Action Against Venturia inaegualis /Apple (Scab on Apple)

4 week old apple seedlings cv. McIntosh are treated with the formulatedtest compound (0.02% active ingredient) in a spray chamber. One dayafter application apple plants are inoculated by spraying a sporesuspension (4×10⁵ conidia/ml) on the test plants. After an incubationperiod of 4 days at 21° C. and 95% r. h. the plants are placed for 4days at 21° C. and 60% r. h. in a greenhouse. After another 4 dayincubation period at 21° C. and 95% r. h. the disease incidence isassessed.

Compounds of Tables 1 to 10 show good activity in this test. Thecompounds 1.24, 1.50, 2.1, 2.7, 2.9, 2.15, 2.42, 2.56, 2.62, 2.68, 2.75,2.85, 2.91, 3.1, 3.8, 3.28, 3.67, 3.74, 10.3 and 10.10 exhibit strongefficacy (<20% infestation).

Example B-4 Action Against Erysiphe graminis /Barley (Powdery Mildew onBarley)

1 week old barley plants cv. Express are treated with the formulatedtest compound (0.02% active ingredient) in a spray chamber. One dayafter application barley plants are inoculated by shaking powdery mildewinfected plants above the test plants. After an incubation period of 6days at 20° C./18° C. (day/night) and 60% r. h. in a greenhouse thedisease incidence is assessed.

Compounds of Tables 1 to 10 show good activity in this test. Thecompounds 1.24, 1.50, 2.1, 2.7, 2.9, 2.15, 2.42, 2.56, 2.62, 2.68, 2.75,2.85, 2.91, 3.1, 3.8, 3.28, 3.67, 3.74, 10.3 and 10.10 exhibit strongefficacy (<20% infestation).

Example B-5 Action Against Botrytis cinerea /Apple (Botrytis on AppleFruits)

In an apple fruit cv. Golden Delicious 3 holes are drilled and eachfilled with 30 μl droplets of the formulated test compound (0.002%active ingredient). Two hours after application 50 μl of a sporesuspension of B. cinerea (4×10⁵ conidia/ml) are pipetted on theapplication sites. After an incubation period of 7 days at 22° C. in agrowth chamber the disease incidence is assessed.

Compounds of Tables 1 to 10 show good activity in this test. Thecompounds 1.24, 1.50, 2.1, 2.7, 2.9, 2.15, 2.42, 2.56, 2.62, 2.68, 2.75,2.85, 2.91, 3.1, 3.8, 3.28, 3.67, 3.74, 10.3 and 10.10 exhibit strongefficacy (<20% infestation).

Example B-6 Action Against Botrytis cinerea /Grape (Botrytis on Grapes)

5 week old grape seedlings cv. Gutedel are treated with the formulatedtest compound (0.002% active ingredient) in a spray chamber. Two daysafter application grape plants are inoculated by spraying a sporesuspension (1×10⁶ conidia/ml) on the test plants. After an incubationperiod of 4 days at 21° C. and 95% r. h. in a greenhouse the diseaseincidence is assessed.

Compounds of Tables 1 to 10 show good activity in this test. Thecompounds 1.24, 1.50, 2.1, 2.7, 2.9, 2.15, 2.42, 2.56, 2.62, 2.68, 2.75,2.85, 2.91, 3.1, 3.8, 3.28, 3.67, 3.74, 10.3 and 10.10 exhibit strongefficacy (<20% infestation).

Example B-7 Action Against Botrytis cinerea /Tomato (Botryis onTomatoes)

4 week old tomato plants cv. Roter Gnom are treated with the formulatedtest compound (0.002% active ingredient) in a spray chamber. Two daysafter application tomato plants are inoculated by spraying a sporesuspension (1×10⁵conidia/ml) on the test plants. After an incubationperiod of 4 days at 20° C. and 95% r. h. in a growth chamber the diseaseincidence is assessed.

Compounds of Tables 1 to 10 show good activity in this test. Thecompounds 1.24, 1.50, 2.1, 2.7, 2.9, 2.15, 2.42, 2.56, 2.62, 2.68, 2.75,2.85, 2.91, 3.1, 3.8, 3.28, 3.67, 3.74, 10.3 and 10.10 exhibit strongefficacy (<20% infestation).

Example B-8 Action Against Pyrenophora teres /Barley (Net Blotch onBarley)

1 week old barley plants cv. Express are treated with the formulatedtest compound (0.002% active ingredient) in a spray chamber. Two daysafter application barley plants are inoculated by spraying a sporesuspension (3×10⁴ conidia/ml) on the test plants. After an incubationperiod of 2 days at 20° C. and 95% r. h. plants are kept for 2 days at20° C. and 60% r. h. in a greenhouse. The disease incidence is assessed4 days after inoculation. Compounds of Tables 1 to 10 show good activityin this test. The compounds 1.24, 1.50, 2.1, 2.7, 2.9, 2.15, 2.42, 2.56,2.62, 2.68, 2.75, 2.85, 2.91, 3.1, 3.8, 3.28, 3.67, 3.74, 10.3 and 10.10exhibit strong efficacy (<20% infestation).

Example B-9 Action Against Septoria nodorum /Wheat (Septoria Leaf Spoton Wheat)

1 week old wheat plants cv. Arina are treated with the formulated testcompound (0.02% active ingredient) in a spray chamber. One day afterapplication wheat plants are inoculated by spraying a spore suspension(5×10⁵ conidia/ml) on the test plants. After an incubation period of 1day at 20° C. and 95% r. h. plants are kept for 10 days at 20° C. and60% r.h. in a greenhouse. The disease incidence is assessed 11 daysafter inoculation.

Compounds of Tables 1 to 10 show good activity in this test. Thecompounds 1.24, 1.50, 2.1, 2.7, 2.9, 2.15, 2.42, 2.56, 2.62, 2.68, 2.75,2.85,2.91, 3.1, 3.8, 3.28, 3.67, 3.74, 10.3 and 10.10 exhibit strongefficacy (<20% infestation).

1. A carboxamide of the formula I

R₁ is

CH₂CH═CHR₂, CH═C═CHR₂ or COR₃; R₂ is hydrogen, C₁-C₆alkyl,C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₇cycloalkyl,COOC₁-C₄alkyl, COOC₃-C₆alkenyl, COOC₃-C₆alkynyl or CN; R₃ is C₁-C₆alkyl,C₁-C₆alkyl substituted by halogen, C₁-C₆alkoxy or C₁-C₆haloalkoxy; or isC₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkoxy, C₁-C₆haloalkoxy;C₃-C₆alkenyloxy or C₃-C₆haloalkenyloxy; C₃-C₆alkynyloxy orC₃-C₆haloalkynyloxy; R₄ is methyl, CF₂Cl, CF₃, CF₂H, CFH₂, Cl or Br; R₅is methyl, CF₃, CH₂OCH₃ or CH₂OCF₃; R₆ is hydrogen, fluoro, CF₃ ormethyl; R₇ is hydrogen, methyl or halogen; and Z is phenyl, halophenyl,C₅-C₇cycloalkyl, C₅-C₇cycloalkyl substituted by C₁-C₃alkyl,C₁-C₃haloalkyl or halogen, or a group of the form

wherein R₈, R₉ and R₁₀ are independently of each other C₁-C₃alkyl.
 2. Acompound of formula I according to claim 1, wherein R₂ is hydrogen,C₁-C₄alkyl, C₁-C₄haloalkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, C₃-C₆cycloalkyl,COOC₁-C₄alkyl, COOC₃-C₄alkenyl or COOC₃-C₄alkynyl; R₃ is C₁-C₆alkyl,C₁-C₆alkyl substituted by fluoro, chloro, bromo, C₁-C₆alkoxy orC₁-C₆haloalkoxy; or is C₁-C₄alkoxy , C₁-C₄haloalkoxy; C₃-C₄alkenyloxy orC₃-C₆haloalkynyloxy.
 3. A compound of formula I according to claim 2,wherein Q is Q1.
 4. A compound of formula I according to claim 3,wherein Z is phenyl, halophenyl or a group of the form

wherein R₈, R₉ and R₁₀ are independently of each other C₁-C₃alkyl.
 5. Acompound of formula I according to claim 3, wherein Z is C₅-C₇cycloalkylunsubstituted or substituted by C₁-C₃alkyl, C₁-C₃haloalkyl or halogen.6. A compound of formula I according to claim 2, wherein Q is Q5 or Q6.7. A compound of formula I according to claim 2, wherein Q is Q2, Q3 orQ4.
 8. A compound of formula according to claim 2, wherein Q is Q1 orQ6; and Z is phenyl, halophenyl or C₅-C₇cycloalkyl unsubstituted orsubstituted by C₁-C₃alkyl, C₁-C₃haloalkyl or halogen.
 9. A compoundaccording to claim 1, selected from the group consisting1-methyl-4-trifluoromethyl-pyrazole-3-carboxylic acid(2-methoxyacetyl)-[2′(4-fluorophenyl)phenyl]amide,1-methyl-4-trifluoromethyl-pyrazole-3-carboxylic acid(2-methoxyacetyl)-[2′(4-chlorophenyl)phenyl]amide,1-methyl-4-trifluoromethyl-pyrazole-3-carboxylic acid(2-propargyl)-[2′(4-fluorophenyl)phenyl]amide,1-methyl-4-trifluoromethyl-pyrazole-3-carboxylic acid(2-propargyl)-[2′(4-chlorophenyl)phenyl]amide,1-methyl-4-trifluoromethyl-pyrazole-3-carboxylic acid(2-acetyl)-[2′(4-fluorophenyl)phenyl]amide,1-methyl-4-trifluoromethyl-pyrazole-3-carboxylic acid(2-acetyl)-[2′(4-chlorophenyl)phenyl]amide,1-methoxymethyl-4-trifluoromethyl-pyrazole-3-carboxylic acid(2-methoxyacetyl)-[2′(4-fluorophenyl)phenyl]amide,1-methoxymethyl-4-trifluoromethyl-pyrazole-3-carboxylic acid(2-methoxyacetyl)-[2′(4-chlorophenyl)phenyl]amide,1-methoxymethyl-4-trifluoromethyl-pyrazole-3-carboxylic acid(2-propargyl)-[2′(4-fluorophenyl)phenyl]amide,1-methoxymethyl-4-trifluoromethyl-pyrazole-3-carboxylic acid(2-propargyl)-[2′(4-chlorophenyl)phenyl]amide,1-methoxymethyl-4-trifluoromethyl-pyrazole-3-carboxylic acid(2-acetyl)-[2′(4-fluorophenyl)phenyl]amide,1-methoxymethyl-4-trifluoromethyl-pyrazole-3-carboxylic acid(2-acetyl)-[2′(4-chlorophenyl)phenyl]amide,1-methyl-4-difluoromethyl-pyrazole-3-carboxylic acid(2-methoxyacetyl)-[2′(4-fluorophenyl)phenyl]amide,1-methyl-4-difluoromethyl-pyrazole-3-carboxylic acid(2-methoxyacetyl)-[2′(4-chlorophenyl)phenyl]amide,1-methyl-4-difluoromethyl-pyrazole-3-carboxylic acid(2-propargyl)-[2′(4-fluorophenyl)phenyl]amide,1-methyl-4-difluoromethyl-pyrazole-3-carboxylic acid(2-propargyl)-[2′(4-chlorophenyl)phenyl]amide,1-methyl-4-difluoromethyl-pyrazole-3-carboxylic acid(2-acetyl)-[2′(4-fluorophenyl)phenyl]amide,1-methyl-4-difluoromethyl-pyrazole-3-carboxylic acid(2-acetyl)-[2′(4-chlorophenyl)phenyl]amide,1-methoxymethyl-4-difluoromethyl-pyrazole-3-carboxylic acid(2-methoxyacetyl)-[2′(4-fluorophenyl)phenyl]amide,1-methoxymethyl-4-difluoromethyl-pyrazole-3-carboxylic acid(2-methoxyacetyl)-[2′(4-chlorophenyl)phenyl]amide,1-methoxymethyl-4-difluoromethyl-pyrazole-3-carboxylic acid(2-propargyl)-[2′(4-fluorophenyl)phenyl]amide,1-methoxymethyl-4-difluoromethyl-pyrazole-3-carboxylic acid(2-propargyl)-[2′(4-chlorophenyl)phenyl]amide,1-methoxymethyl-4-difluoromethyl-pyrazole-3-carboxylic acid(2-acetyl)-[2′(4-fluorophenyl)phenyl]amide, and1-methoxymethyl-4-difluoromethyl-pyrazole-3-carboxylic acid(2-acetyl)-[2′(4-chlorophenyl)phenyl]amide.
 10. A fungicidal compositioncomprising the compound as claimed in claim 1, together with a suitablecarrier, capable of for controlling a microorganism selected from thegroup consisting of Puccinia recondita, Podosphaera leucotricha,Venturia inaequalis, Erysiphe graminis, Botrytis cinerea, Pyrenophorateres and Septoria nodorum.
 11. A method of controlling infestation ofcultivated plants by microorganisms selected from the group consistingof Puccinia recondite, Podosphaera leucotricha, Venturia inaequalis,Erysiphe graminis, Botrytis cinerea, Pyrenophora teres and Septorianodorum, comprising application to the plants, parts thereof or thelocus thereof of a composition comprising the compound as claimed inclaim 1.